NP-MRD: Showing NP-Card for 20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione (NP0321692)

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Record Information

Version

2.0

Created at

2022-09-12 00:02:03 UTC

Updated at

2022-09-12 00:02:03 UTC

NP-MRD ID

NP0321692

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione

Description

20-Acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]Docosa-3,9,11-triene-8,19-dione belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione is found in Talaromyces cecidicola. Based on a literature review very few articles have been published on 20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]Docosa-3,9,11-triene-8,19-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202022D          

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M  END

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  Mrv1652309122202022D          

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M  END
> <DATABASE_ID>
NP0321692

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2=C(C(O)=CC3=C2CC2C(C)(CCC4C(C)(C)C(=O)C(CC24C)C(C)=O)O3)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O6/c1-13-9-16-15-10-21-26(5)12-17(14(2)28)23(30)25(3,4)20(26)7-8-27(21,6)33-19(15)11-18(29)22(16)24(31)32-13/h11,13,17,20-21,29H,7-10,12H2,1-6H3

> <INCHI_KEY>
DPIJZZQCJNEDHA-UHFFFAOYSA-N

> <FORMULA>
C27H34O6

> <MOLECULAR_WEIGHT>
454.563

> <EXACT_MASS>
454.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.164567699034805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{17,22}]docosa-3(12),4(9),10-triene-8,19-dione

> <JCHEM_LOGP>
5.7554805666666695

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.92068113937407

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.256216464673049

> <JCHEM_PKA_STRONGEST_BASIC>
-4.018783894703938

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
123.54959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{17,22}]docosa-3(12),4(9),10-triene-8,19-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.529  -1.447   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -9.519   0.267   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -9.336   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   28                                             
CONECT    7    6                                                            
CONECT    8    6    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21                                                            
CONECT   23   11   24                                                       
CONECT   24   23    8   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    6   29                                                  
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29    4   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₆

Average Mass

454.5630 Da

Monoisotopic Mass

454.23554 Da

IUPAC Name

20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{17,22}]docosa-3(12),4(9),10-triene-8,19-dione

Traditional Name

20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{17,22}]docosa-3(12),4(9),10-triene-8,19-dione

CAS Registry Number

Not Available

SMILES

CC1CC2=C(C(O)=CC3=C2CC2C(C)(CCC4C(C)(C)C(=O)C(CC24C)C(C)=O)O3)C(=O)O1

InChI Identifier

InChI=1S/C27H34O6/c1-13-9-16-15-10-21-26(5)12-17(14(2)28)23(30)25(3,4)20(26)7-8-27(21,6)33-19(15)11-18(29)22(16)24(31)32-13/h11,13,17,20-21,29H,7-10,12H2,1-6H3

InChI Key

DPIJZZQCJNEDHA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Talaromyces cecidicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpenoid
Diterpene lactone
Xanthene
Naphthopyran
Dibenzopyran
2-benzopyran
1-benzopyran
Naphthalene
Isochromane
Benzopyran
Chromane
1-hydroxy-2-unsubstituted benzenoid
1,3-diketone
Alkyl aryl ether
Benzenoid
1,3-dicarbonyl compound
Pyran
Vinylogous acid
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.76	ChemAxon
pKa (Strongest Acidic)	8.26	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	123.55 m³·mol⁻¹	ChemAxon
Polarizability	50.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163074104

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione (NP0321692)

MOL for NP0321692 (20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione)

3D MOL for NP0321692 (20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione)

3D SDF for NP0321692 (20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione)

3D-SDF for NP0321692 (20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione)

PDB for NP0321692 (20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione)

3D PDB for NP0321692 (20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione)

SMILES for NP0321692 (20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione)

INCHI for NP0321692 (20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione)

Structure for NP0321692 (20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione)

3D Structure for NP0321692 (20-acetyl-10-hydroxy-6,14,18,18,22-pentamethyl-7,13-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-3(12),4(9),10-triene-8,19-dione)